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Let's say we have a modal with a number of similar actions. We're trying to decide whether a mass action to mark/clear all checkboxes is justified. The modal performs an infrequent action in the system, used maybe a few times a day by a professional user who works with the system for a couple hours a day.

The users would naturally like to have this mass action, because it "saves time" and because they're unaware of the downsides, like visual clutter, increased cognitive load and the general pettiness of trying to save every possible click.

And at a certain number of controls it does appear to be worth it. How can we determine where to draw this line?

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By testing it. Find out whats the most common amount of selected options and change your form according to that.

If 90% of the people select 100% of the given values then you could preselect them all and add a "Deselect all" option which changes to "Select all" after deselecting everything.

On the other hand if most people just select 2-3 values then "Select all" would not be justified because of the reasons you already named.

If your users "naturally would like" to have this option then give them that option in the best way possible.

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